Process Development and Scale-Up of a Novel Route to 8-Aminooctanoic Acid

A robust and scalable process for the production of 8-aminooctanoic acid has been developed. Starting from commercially available azelaic acid, the target compound was obtained in four steps in a 62% overall yield. The process starts with a Fischer esterification, followed by a highly selective enzymatic hydrolysis of dimethyl azelate to methyl hydrogen azelate. Ammonolysis of the latter using aqueous ammonia and subsequent Hofmann rearrangement yields 8-aminooctanoic acid. The scalability of the process has been demonstrated through the successful production of 25 kg of 8-aminooctanoic acid (5 kg batches). Furthermore, a proof of principle has been demonstrated for a further streamlined process in which the first three steps are telescoped.